30+ Ways to Celebrate Valentines Day, Chicago Style

So. I know I’ve said this before, and hate us if you will, but we love Valentine’s Day.

Any excuse to go out (dress up!) and spend quality time together is a win in our book.

I always get lot’s of questions around this time of year asking for restaurant recommendations and ideas for things to do to celebrate the holiday, so I wanted to refresh this post with our big list of favorites–whether you’re celebrating Galentine’s with your best girlfriends or with your significant other, I promise you’ll find a lot of Valentine’s Day Chicago inspiration in this list 😉

(Or, let’s be honest, this is a really good list for any other day besides Valentine’s Day too!) I linked to all these Google Maps locations so you can star away until your heart is content!

Valentine’s Day Events + Fun Date Ideas:

Valentine’s Day in Chicago:

Valentines Day Pasta Making Class at Eataly: Eataly is one of my FAVORITE places in the city, and they have a really fun pasta making class on Valentine’s Day! It includes wine pairings and a multi-course meal! Would be such a fun activity for a date or with girlfriends!

“Naked at the Art Museum” Scavenger Hunt: This would be a HILARIOUS thing to do with your girlfriends–tour group, Watson Adventures offers a very, um, different sort of art tour of Chicago’s Art Institute, focusing on nude art 😂 The website says, “You’ll scrutinize bathing beauties, peeping Toms, sultry sirens, a muscleman who’ll ruin his birthday suit while wrestling a lion, a woman enjoying a golden shower from Zeus, cads and cuckolds, provocative Picassos, dangerous natives, a mystic who has gone too far with the Slim-Fast, and much more!”

Skate night at Chicago Athletic Association: On the 14th and 15th, the Chicago Athletic Association is hosting roller skating nights with a live DJ spinning throwback jams! This sounds like such a fun thing to do with a group!

Valentines Day Chicago Date Ideas:

Dinner, drinks, and music at Thalia Hall: Thalia Hall in Pilsen is basically like “building crawl”–it has so many cool bars in it! Do dinner at Duseks, and drinks at The Tack Room, Punch House, and/or catch a concert at Thalia Hall!

Neighborhood crawl: Our friend Jax suggested this fun idea: pick a fun new-to-you neighborhood and do cocktails at one spot, apps at another, entree at another, and post-dinner drinks at another! It’s a fun way to explore and try a bunch of different things!

Walk along the Lake Michigan Lakefront Trail:I mean, that is if it’s not below zero. There are few things more beautiful than the icy, peaceful lakefront in the winter! (If you can feel your face 😉). Start at North Avenue Beach and walk South. Grab a drink at The Drake Hotel’s historic old-school bar, Coq d’Or afterwords to warm back up!

Chicago Art Institute: One of my personal favorite activities for a cold day. I’m not sure what it is, but there’s something about an art museum that’s just really romantic. End with a glass of wine at Terzo Piano, which overlooks the park! Plus, you can explore downtown Chicago before or after!

Maggie Daley Ice Skating Ribbon: If you can brave the cold, Maggie Daley park’s skating “ribbon” is such a fun spot for ice skating downtown! You get great views of the skyline, too!

Cooking classes: There are tons of options for cooking classes in Chicago! I shared a bunch over in this post!

Aire Ancient Baths: We’ve only done this once but LOVEDDDD our experience here. It’s not terribly expensive (at least compared to a couples massage) and it was as fun as it was relaxing! Would highly recommend doing with a significant other or with girlfriends!

Chicago Valentine’s Day Restaurants–Best Dinner Spots:

Nando Milano Trattoria: Our favorite tiny, cozy Italian restaurant that we just discovered this year. The pasta there is better than many of the places we had in Italy–it’s VERY authentic and we adore everyone who works there. Make sure to tell the Maitre’d, Lucca, we sent you (he’s one of my favorite people ever) and if Umberto is your server (LOVE him and he also happens to be Lucca’s cousin) tell him we say hi as well! 🙂 My favorite dishes there are the rigatoni and the fettuccini bolognese–their specials are ALWAYS spot on as well. Let Lucca pick your wine! Also, the Panna Cotta is one of my favorite desserts of all time! Doesn’t look like much, but it’s to die for. You really feel the Italian love here that you rarely get in the states!

Boufhaus: Our #1 favorite Chicago restaurant. (Okay, it’s probably tied with Nando, but you can’t compare the two.) Another place we love to sit at the bar–the bartenders are always amazing and are so knowledgable! The service is always incredible–if you go back more than once, they’ll remember you. The steak is unreal–and I’m not usually a big meat person. It’s definitely not a stuffy “steakhouse” vibe, more like a cozy, casual bistro, but they are very well-known for their meat.

Make sure to start with their seasonal market salad–a bunch of freshly shaved root veggies with the most amazing dressing–or the crudité–which is basically the most incredible veggies and dip you’ve ever tasted. Split the ribeye for your entree (it’s huge) and get a bunch of sides. Best meal you’ll have in a long, long time. Tell Jessica (she will likely greet you when you walk in!) we sent you! 😘She’s wonderful!

Ada Street: Another one of my favorite restaurants, though we don’t get here often. The seasonal, farm to table fare is incredible as is the staff. It’s a small, cozy, space and I’ve never met anyone who has been disappointed with their meal here!

Tango Sur: One of the most romantic restaurants in Chicago in my opinion! It’s BYOB Argentinian. SO good and very budget-friendly. (The portions are HUGE!) They don’t take resos, so be prepared to wait! Luckily, they have a back waiting room where you can pop open your wine!

Club Lucky: Another Italian favorite, but comparing this to Nando is like comparing apples to oranges. I will say we go to Nando more than Club Lucky, but sometimes we’re in the mood for Club Lucky’s livelier ambiance and their great martinis! I would describe Nando as true Italian (small menu, very authentic Italian feel–no Chicken Parm, Chicken Piccata or Italian green salads) and Club Lucky as Italian American–(and I say that VERY lovingly–as in, they have really big menu with all the Italian American classics–it’s like your childhood best friend’s Italian American Grandma’s Sunday dinner). It’s an old-school diner that serves up home cooked dishes. We love sitting at the bar, but if you’d like a table, they have cozy booths in the front and in the back!

BLVD: A super swanky supper club with an old Hollywood vibe. Definitely go for the steak here too–they serve it with a bunch of different seasoning salts and it’s one of the coolest experiences. If you want something out of the ordinary in terms of your dinner experience, this is it! You feel like a movie star!

Gemini Bistro: I lived across the street for years (look across the street above the bar–see the middle apartment unit? That was my window. Haha!) and it’s always been one of my favorites. They recently revamped it and it’s absolutely beautiful inside. They also make the best sidecars! You can’t go wrong with the steak frites or shortrib ravioli. Go to Barrelhouse Flat after–it’s just a short Uber up the road!

The Rosebud: If you like old school Italian, you can’t get more classic than Rosebud in Little Italy!

Allium at the Four Seasons: One of my favorite Valentine’s Day dates was here and we’ve loved visiting ever since! It’s the restaurant in the Four Seasons–super swanky, old-school, and ultra cozy. The perfect place to be on a cold night. It’s great just for drinks, too!

Eddie V’s Lounge: Sometimes, you just want a classic steakhouse experience, you know? We love Eddie V’s lounge! Their booths are super cozy and the service is wonderful. Neal loves their oysters and the steak is really great (this sounds weird but I hate when a lot of steakhouses char it on the outside–they don’t do that here!) Make sure you order the Bananas Foster for dessert! It’s a great way to end a day of shopping on Michigan Ave!

RM Champagne Salon: OK this is also on the cocktail list, but it’s great for both. I think this MIGHT be the darkest, most romantic, lit only by candles restaurant in Chicago. It’s so pretty, the food is phenomenal. And well, obviously the champs and wine are fantastic 😉A great place for a date, but also for girls night!

Chicago Valentine’s Day Drinks–Best places to go for cocktails:

Margeaux Brasserie: The Waldorf’s new french-inspired bar is drop dead gorgeous, ultra romantic, and our favorite place in the Gold Coast to grab a nightcap. Split some frites, too! If you’re hungry, their duck wings l’orange are so good. (And I don’t even like duck!) I promise I’m not just biased because we got engaged in the circle drive! 😉

Maude’s Liquor Bar: I love this place for cocktails, they’re supposed to have really good food too but we’ve never eaten here!

The Barrelhouse Flat: Neal and I went here when we first started dating and it’s still one of my most favorite nights ever. They have the coolest cocktails with combinations you’d never think to try, and the setting could not be cooler. Make sure to get some of their fancy popcorn to snack on!

The Signature Room: It might sound cheesy, but even after living here for 8 years, I still get butterflies from the view of the city from the 95th floor.

The Up Room at Hotel Robey: One of my favorite favorite places in the city. The Robey’s Up Room offers a truly unique skyline view and one of the only ones you can get from the West Side! Their cocktails are always great, too.

Violet Hour: Another Wicker Park staple that has been around forever, Violet Hour is an experience. It’s known for pouring the most creative cocktails in the city, and it’s dark, quiet, romantic, and no phones allowed!

Gilt Bar downstairs lounge: Gilt Bar is good for dinner, but way better for drinks and live music in their downstairs lounge! Their live Jazz bands always kill it, and the intimate vibe is perfect for a Valentine’s Day date.

RM Champagne Salon: If you ask someone what the most romantic restaurant in Chicago is, they will likely say RM Champagne! It’s truly beautiful, quaint, candles everywhere–and what’s more fun than a champagne bar!? Plus, it’s in West Loop, which is a perfect location for bar hopping!

DrumBar: If you want downtown romance with a buzzing atmosphere and a great city view, DrumBar can’t be beat!

Scofflaw: Want great cocktails and romantic ambience without all the fuss? Scofflaw in Logan Square will be your new go-to! It’s part cocktail bar, part dive bar, with a fireplace and lot’s of little nooks to cozy up in.

The California Clipper: If you want more lively action than romantic vibes, you’ll love the atmosphere of this cocktail lounge in Humboldt Park. You’ll feel like you’ve stepped into the 1930’s, with awesome live music and great old-school cocktails. It is busy, so make sure to bring cash (they don’t take cards) and get there early for any chance at scoring a table! (And make sure you bring a warm coat, there is often a line outside, but I promise it’s worth the wait!)

What are your favorite ways to celebrate Valentines day in Chicago?

I would love to know your ideas! Leave them in the comments below. You guys always have the best ideas!

Downstairs (the Library as it’s known) is GREAT! But If you can’t get in, I’d go right next door to Bavette’s, their downstairs is amazing as well and their upstairs bar/restaurant is quieter than Gilt’s. .

Great suggestions, thank you! Definitely bookmarking this. My husband and I go to Little Goat every year, because it’s where we went for our first Valentine’s Day together. Bullseye french toast, can’t beat it 🙂